Jeremy allowed a few seconds for me to adjust then began fucking me with slow steady strokes. The pain in my ass was still far from being small and I couldn’t get away from the feeling I needed to take a monster dump but that itch was being scratched and the pain was ridden by a wave of pleasure that had me feeling more than a little aroused. My cock was throbbing and dripping cum and he began to pick up the pace, "Fuck my ass, don’t stop, please," and I meant it this time. The pain was no where near as bad as the pleasure was good. He began pumping me like he would an old whore, fucking me hard and fast. I could never figure out why a man would want to be fucked up the ass but I was riding on the edge of an orgasm that threatened to rip me apart. He began grunting then slipped his hands under my ass and pulled me tightly to him as he slammed his cock in and out of my asshole. I could feel his cock grow then he pulled me harder against him and filled my ass with his scum. I needed to cum so bad I thought my nuts would explode and I began jacking my cock, "Get your hand away from there or I will bust your ass good," Annette said loudly.

Jeremy pulled his cock from my ass and walked away. Bobby came over, flipped me onto my stomach with my ass high, spit on my asshole, smeared it around a little then forced half his cock into my asshole. Yes, I had just been fucked by a pretty good sized tube of meat but that didn’t seem to make any difference, I screamed in pain and shoved my face into the mat. As if to make sure he was causing me as much pain as possible he pulled his cock back all the way out and slammed it completely into my battered hole, "Now, lets fuck," he said and began using my asshole for a punching back for his cock. It felt like he was ripping my asshole wide open and he was enjoying every minute of it. He laughed as he slammed into me without regard for the fact that he was tearing and bruising my asshole. He grabbed my hair and wrenched my head back so far that breathing was near impossible and I started blacking out, he let go, allowed be to breathe then grabbed and pulled harder as he slammed my ass. His cock felt like a three inch wide steel bar slamming into my ass. He went on and on, after about five minutes my ass was getting used to his abuse and I felt pleasure rushing in and making my cock hard again and just kept on fucking me. He slammed into my ass so hard I was certain I was bruised, then picked me up like I weighed no more than a bag of potatoes and held me while he fucked me longer and harder, bouncing me around like a puppet. He began to grunt as he slipped his hands to my nipples and dug his nails into the tender flesh. Pain and pleasure were mixed so well together that I could no longer tell them apart. When his cum finally filled my asshole I screamed with each stroke, begging him to make me cum. He threw me on the mat like so much discarded trash and walked away, my cock hard and throbbing, begging for relief.

I lay on the mat panting, trying to catch my breath. My cock was hard, my asshole destroyed and I needed to cum so bad I thought my balls would explode. Mistress Annette squatted next to me, "My, you seem to be enjoying yourself." I looked at her, holding onto my cock, "I need to cum. Please allow me to cum, I will do anything but I need some relief," I gasped. "So, tell me the truth, do you enjoy getting your ass fucked?" I had already been degraded as much as any man could be, admitting this was really no big deal, "Yes…it hurt like hell, but it feels so damn good at the same time." "So, is it the pain you enjoy or the feeling of having your asshole stuffed with a big, hard cock?" she asked. I thought for a minute, it wasn’t really the pain I enjoyed so much as what the pain finally lead to, "I liked having a hard cock in my ass, fucking me like a bitch," I admitted. She wrapped her hand around my hard cock causing it to jump, "Ok, I guess we can take care of this little problem," she said as she squeezed my cock tightly.

She walked away and talked to the three girls who had been watching me turn into a bitch for two men with huge cocks; all four of them approached me. "Jim, you have yet another decision to make. These three girls are here for you to choose from for your next little task…which one will you choose?" asked Annette. All three of the girls were beautiful, all were young…I would happily fucked any one of them, but I had to choose, "I choose Shelly," I said, remembering she had been so nice to me. Mistress Annette laughed, "I thought so. Well, Jim, you may have made a slight mistake, but we will see." Once again I was taken to the wedge shaped mat and placed on my back with my ass at the edge, only this time the wedge was higher and my ass was sticking higher and my still hard cock was right over my face.

"Do you remember what I said the next task would be?" she asked. I thought but, for a moment, could not remember…then it hit me, "Yes, I remember." "So, what is it?" I looked at Shelly, "I am going to get fucked in the ass with a fist," these words were almost choked off with fear. Shelly stepped between my legs and began squeezing gel into my asshole and onto her hand. "Most people who do this start with a few fingers and push the hand into the orifice before closing their hand into a fist; this causes less pain and allows your asshole to stretch slowly. That is not the way we are going to do it. Shelly will work her fist into your asshole then punch your gust from the inside. She will do this until you cum, which may not be easy either. I said you may have made a mistake…if you look at her hands you will notice she has hands almost as large as a man’s. Second, Shelly can seem like an angel, but she is far from it, unlike the other girls who do my bidding she actually assists me willingly and enjoys inflicting pain as much as I do. If you think about it, she was the one who got you to touch her the first day, she is also the one who struck you the most and hardest with the cane and whip. I have a feeling you will wish you had made another choice. On the other hand, she may well be the best to relieve your pressure issue," she smiled as she walked away.

Shelly began pressing against my opened asshole with her fist, it felt like she was trying to force a grapefruit up my ass. She began twisting her fist back and fort while applying pressure, "I was hoping you would choose me, the other girls just don’t get into this the way I do. I am going to ram my fist so deep in your ass you will never forget me and while I am fucking your ass with my fist I will allow you to jack your cock. Your job is to cum…in your mouth, every drop I see miss your mouth will mean another two minutes of fisting your ass…catch it all and I will stop when you cum." The whole time she was talking she was applying more and more pressure, twisting and pressing until I could feel her fist almost pushing through the muscular ring, then she pushed hard and fast. Her fist popped into my battered asshole and I screamed in pain and tried to breathe. The pain was worse that I had expected…I had been fucked, fucked and fucked again by some very large cocks, I was certain this would not be so painful…wrong again. She pressed slowly but forcefully deeper into my far from virgin hole causing my bowels to cramp badly…this was but the beginning.

Once she reached the end of my dark tunnel she began pulling back out, it felt like she was dragging my guts out of my asshole, but the pressure was less. She pulled her fist all the way out, greased it up again and slammed it back into my asshole. Pain shot through my body as she drove deep into my gut, then began punching. My cock was still stone hard and I began jacking it as she started punching deep in my asshole and backing out, almost in rhythm with my strokes. As my cock began dripping precum I made sure my mouth was under it to catch every drop. Once again she pulled her hand from my ass then shoved it in again, then again and again. Pain was becoming almost as desirable as pleasure and both were building fast. With her fist deep in my asshole she began sliding her fingers along her arm and into my asshole…fire like pain burned in my asshole as raging pleasure began to take over my body. She was stretching my asshole still more but she couldn’t get her other hand in. My balls began to rumble and I knew I was seconds from cuming. My whole body was shaking and my asshole spasmed around her arm as she continued fisting me. Cum shot from my cock like it was coming from a fire hose; I kept my mouth open and captured most of it. That was the first time I had eaten my own cum…but it surely would not be the last. My body went limp as she continued fucking my ass, I really didn’t care. The last thing I remember was her removing her fist from my asshole with a pop, then the lights went out.

This story was taken from one these sites, check them out to find more sex stories:

https://tophindisexvideo.com/en/category/1900600/toy/popular/1

https://hentaivideostube.org/en/video/13554958834554552512

https://twinksex.org/en/category/4330356743/coach/popular/1

https://indianpornotube.org/en/category/6094904/uniform/popular/1

https://vatertochterporno.com/de/category/7340133/couple/popular/1

https://indiansexvideotube.net/en/category/3407928/bhabhi/popular/1

https://cuckoldtubes.net/en/video/2705852731054333383

https://twinkdick.net/en/category/4335730695/oral/popular/1

https://forcedgaysextube.com/en/video/3824942640594968887

https://pornarab.org/en/category/210960387/desi/popular/1